Publication details

Stereocontrolled Synthesis of Pseurotin A(2)

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Authors

JACHAK Gorakhnath R. THARRA Prabhakara R. SEVELDA Petr ŠVENDA Jakub

Year of publication 2021
Type Article in Periodical
Magazine / Source Journal of Organic Chemistry
MU Faculty or unit

Faculty of Science

Citation
Web https://doi.org/10.1021/acs.joc.1c01152
Doi http://dx.doi.org/10.1021/acs.joc.1c01152
Keywords Mixtures; Organic compounds; Anions; Solutions; Ethyl groups
Description We report synthesis of two diastereomeric structures previously proposed for the complex secondary metabolite pseurotin A(2). Both structures were accessed from the same building blocks taking advantage of a stereodivergent nickel(II)-iamine-catalyzed 1,4-addition of a chiral 2-alkoxycarbonyl-3(2H)-furanone. Late-stage Csp-Csp(3) cross-coupling of a highly functionalized bromoalkyne featured in the pseurotin A(2) side-chain assembly. The work supports the 2016 stereochemical revision of pseurotin A(2) and represents the first chemical synthesis of this natural product.
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